Showing Compound Succinic acid (FDB001931)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:10 UTC

Update date

2020-09-17 15:42:08 UTC

Primary ID

FDB001931

Secondary Accession Numbers

FDB031187

Chemical Information

FooDB Name

Succinic acid

Description

Succinic acid is a four-carbon acyclic dicarboxylic acid. It is a white, odorless solid with a highly acidic taste. It is used as a flavoring agent, contributing a sour and astringent component characteristic of the umami taste (PMID:21932253). The anion, succinate, is a key component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in mitochondrial function, being both part of the respiratory chain and the Krebs cycle. SDH, with a covalently attached FAD prosthetic group, is able to bind several different enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the entire Krebs cycle. Succinic acid has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid is also a microbial metabolite. Indeed, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter sp., Acinetobacter sp., Proteus mirabilis, Citrobactes frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid, or its anion succinate, is used as an excipient in pharmaceutical products to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. In 2004, succinic acid was identified by the Department of Energy of the United States of America as one of twelve molecules that can be produced from plant sugars through biological or chemical processes and that have a potential to subsequently be converted to a number of high-value bio-based chemicals or materials.

CAS Number

110-15-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Ethanedicarboxylate	biospider
1,2-Ethanedicarboxylic acid	biospider
1,4-Butanedioate	biospider
1,4-Butanedioic acid	biospider
1,4-BUTANEDIOIC ACID (SUCCINIC ACID)	biospider
1cze	biospider
Acid of amber	biospider
Acide butanedioique	ChEBI
Acide succinique	ChEBI
Acidum succinicum	biospider
Amber acid	db_source
Amber acid, butanedioic acid, ethylenesuccinic acid	biospider
Ammonium succinate	biospider
Asuccin	biospider
Bernsteinsaeure	ChEBI
Butandisaeure	ChEBI
Butanedioic acid	biospider
Butanedioic acid (9CI)	biospider
Butanedioic acid diammonium salt	biospider
Butanedioic acid, 9CI	db_source
Butanedionate	Generator
Butanedionic acid	biospider
Dihydrofumarate	biospider
Dihydrofumaric acid	biospider
E363	db_source
Ethane-1,2-dicarboxylic acid	db_source
Ethanedicarboxylic acid	biospider
Ethylene dicarboxylic acid	biospider
Ethylene succinic acid	biospider
Ethylenesuccinate	Generator
Ethylenesuccinic acid	biospider
FMR	biospider
HOOC-CH2-CH2-COOH	biospider
Katasuccin	biospider
MAE	biospider
Potassium succinate	biospider
Sal succini	biospider
Salt of amber	biospider
SIN	biospider
Spirit of amber	biospider
SUC	biospider
SUCC	biospider
Succinate	biospider
succinate, 9	biospider
Succinellite	biospider
Succinic acid (8CI)	biospider
Succinic acid, acs	biospider
Succinicum acidum	biospider
Succinicun acidum	biospider
Wormwood	biospider
Wormwood acid	db_source

Predicted Properties

Not Available

Chemical Formula

C4H6O4

IUPAC name

InChI Identifier

InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

InChI Key

KDYFGRWQOYBRFD-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCC(O)=O

Average Molecular Weight

118.088

Monoisotopic Molecular Weight

118.02660868

Classification

Not classified

Ontology

Gastrointestinal disorders:

Diarrhea

Cardiac disorders:

Cardiomyopathy

Cancer:

Lung cancer

Ingestion

Trace element

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.68%; H 5.12%; O 54.19%	DFC
Melting Point	Mp 184-185°	DFC
Boiling Point	Bp 235° dec.	DFC
Experimental Water Solubility	83.2 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	-0.59	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 5.7 (25°, H2O)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Not Available

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15741

Phenol-Explorer ID

Not Available

DrugBank ID

DB00139

HMDB ID

HMDB00254

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1040431

SuperScent ID

1110

Wikipedia ID

Succinic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
additive	64047	Any substance which is added to food to preserve or enhance its flavour and/or appearance.	DUKE
anti feedant			DUKE
bruchiphobe			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
dye	37958		DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sour	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.